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【结 构 式】

【分子编号】38594

【品名】benzhydryl 2-chloro-2-[(2R,3S)-2-[3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]-2-oxopropoxy]-4-oxo-3-[(2-phenylacetyl)amino]azetidinyl]acetate

【CA登记号】

【 分 子 式 】C31H29ClN6O6S

【 分 子 量 】649.1268

【元素组成】C 57.36% H 4.5% Cl 5.46% N 12.95% O 14.79% S 4.94%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XVI)

The partial hydrogenation of (VIII) with H2 over Pd/(CaCO3) in methanol gives the allyl ether (IX), which is epoxidized with MCPBA in dichloromethane yielding epoxide (X). Epoxide cleavage with the lithium salt of 1-methyltetrazole-5-thiol (XI) in THF affords the isopropanol derivative (XII), which is oxidized with CrO3/H2SO4 in acetone giving the ketone (XIII). The ozonolysis of the isopropylidene group of (XIII) with O3 in dichloromethane affords the alpha ketoester (XIV), which is reduced with Zn/AcOH to the alpha hydroxyester (XV). The reaction of (XV) with SOCl2 and pyridine affords the alpha chloroester (XVI), which by reaction with triphenylphosphine in refluxing dichloromethane gives the alpha triphenylphosphoranylidene acetate (XVII). Thermal cyclization of (XVII) in refluxing dioxane affords the oxacephem derivative (XVIII), which is deacylated by reaction with PCl5 and pyridine providing the 7-beta-amino oxacephem derivative (XIX).

1 Narisada, M.; et al.; Synthetic studies on beta-lactam antibiotics. Part 10. Synthesis of 7beta-[2-carboxy-2-(4-hydroxyphenyl)acetamido]-7alpha-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-1-oxa-1-dethia-3-cephem-4-carboxylic acid disodium salt (6059-S) and its related. J Med Chem 1979, 22, 7, 757.
2 Nagata, W.; Narisada, M. (Shionogi & Co. Ltd.); Arylmalonamido-1-oxadethiacephalosporins. US 4180571 .
3 Narisada, M.; Nagata, W. (Shionogi & Co. Ltd.); Arylmalonamido-1-oxadethiacephalosporins. DE 2713370; US 4138486 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIII) 38586 1-phenylethyl 3-methyl-2-[(3S,4R)-2-oxo-3-[(2-phenylacetyl)amino]-4-(2-propynyloxy)azetidinyl]-2-butenoate C27H28N2O5 详情 详情
(IX) 38587 benzhydryl 2-[(2R,3S)-2-(allyloxy)-4-oxo-3-[(2-phenylacetyl)amino]azetidinyl]-3-methyl-2-butenoate C32H32N2O5 详情 详情
(X) 38588 benzhydryl 3-methyl-2-[(2R,3S)-2-(2-oxiranylmethoxy)-4-oxo-3-[(2-phenylacetyl)amino]azetidinyl]-2-butenoate C32H32N2O6 详情 详情
(XI) 38589   C2H3LiN4S 详情 详情
(XII) 38590 benzhydryl 2-[(2R,3S)-2-[2-hydroxy-3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]propoxy]-4-oxo-3-[(2-phenylacetyl)amino]azetidinyl]-3-methyl-2-butenoate C34H36N6O6S 详情 详情
(XIII) 38591 benzhydryl 3-methyl-2-[(2R,3S)-2-[3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]-2-oxopropoxy]-4-oxo-3-[(2-phenylacetyl)amino]azetidinyl]-2-butenoate C34H34N6O6S 详情 详情
(XIV) 38592 benzhydryl 2-[(2R,3S)-2-[3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]-2-oxopropoxy]-4-oxo-3-[(2-phenylacetyl)amino]azetidinyl]-2-oxoacetate C31H28N6O7S 详情 详情
(XV) 38593 benzhydryl 2-hydroxy-2-[(2R,3S)-2-[3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]-2-oxopropoxy]-4-oxo-3-[(2-phenylacetyl)amino]azetidinyl]acetate C31H30N6O7S 详情 详情
(XVI) 38594 benzhydryl 2-chloro-2-[(2R,3S)-2-[3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]-2-oxopropoxy]-4-oxo-3-[(2-phenylacetyl)amino]azetidinyl]acetate C31H29ClN6O6S 详情 详情
(XVII) 38595 benzhydryl 2-[(2R,3S)-2-[3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]-2-oxopropoxy]-4-oxo-3-[(2-phenylacetyl)amino]azetidinyl]-2-(triphenylphosphoranylidene)acetate C49H43N6O6PS 详情 详情
(XVIII) 38596 benzhydryl (6R,7S)-3-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-8-oxo-7-[(2-phenylacetyl)amino]-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C31H28N6O5S 详情 详情
(XIX) 38597 benzhydryl (6R,7S)-7-amino-3-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C23H22N6O4S 详情 详情
Extended Information